J. Am. Chem. Soc., 125, 8096-8097 (2003).

2003 American Chemical Society

Intramolecular Nucleophile-induced Photorearrangements and Silene Formation from an ortho-(methoxymethyl)phenylsilacyclobutane

William J. Leigh* and Xiaojing Li

Contribution from the Department of Chemistry, McMaster University, Hamilton, ON  Canada  L8S 4M1

Abstract: Direct photolysis of 1-(ortho-(methoxymethyl)phenyl)-1-phenylsilacyclobutane yields three isomeric products attributed to intramolecular trapping of an initially formed silicon-carbon biradical intermediate by migration of the benzylic methoxy group to silicon, along with the (expected) intramolecularly ether-stabilized silene due to formal [2+2]-cycloreversion.

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